MXPA01009881A - Ligandos de receptores de melanocortina. - Google Patents
Ligandos de receptores de melanocortina.Info
- Publication number
- MXPA01009881A MXPA01009881A MXPA01009881A MXPA01009881A MXPA01009881A MX PA01009881 A MXPA01009881 A MX PA01009881A MX PA01009881 A MXPA01009881 A MX PA01009881A MX PA01009881 A MXPA01009881 A MX PA01009881A MX PA01009881 A MXPA01009881 A MX PA01009881A
- Authority
- MX
- Mexico
- Prior art keywords
- heteroaryl
- hydrogen
- alkyl
- aryl
- heterocycloalkyl
- Prior art date
Links
- 239000003446 ligand Substances 0.000 title abstract description 12
- 108090000950 Melanocortin Receptors Proteins 0.000 title description 11
- 102000004378 Melanocortin Receptors Human genes 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 110
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 20
- 238000011282 treatment Methods 0.000 claims abstract description 16
- 201000010099 disease Diseases 0.000 claims abstract description 10
- 208000035475 disorder Diseases 0.000 claims abstract description 10
- 208000008589 Obesity Diseases 0.000 claims abstract description 8
- 235000020824 obesity Nutrition 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 230000037396 body weight Effects 0.000 claims abstract description 5
- 206010061218 Inflammation Diseases 0.000 claims abstract description 4
- 230000004054 inflammatory process Effects 0.000 claims abstract description 4
- 230000015654 memory Effects 0.000 claims abstract description 4
- 210000005036 nerve Anatomy 0.000 claims abstract description 4
- 230000008439 repair process Effects 0.000 claims abstract description 4
- 206010006895 Cachexia Diseases 0.000 claims abstract description 3
- 206010028289 Muscle atrophy Diseases 0.000 claims abstract description 3
- 206010040047 Sepsis Diseases 0.000 claims abstract description 3
- 206010040070 Septic Shock Diseases 0.000 claims abstract description 3
- 201000001880 Sexual dysfunction Diseases 0.000 claims abstract description 3
- 208000022531 anorexia Diseases 0.000 claims abstract description 3
- 230000009084 cardiovascular function Effects 0.000 claims abstract description 3
- 206010061428 decreased appetite Diseases 0.000 claims abstract description 3
- 230000012010 growth Effects 0.000 claims abstract description 3
- 230000009593 intrauterine fetal growth Effects 0.000 claims abstract description 3
- 230000020763 muscle atrophy Effects 0.000 claims abstract description 3
- 201000000585 muscular atrophy Diseases 0.000 claims abstract description 3
- 230000036303 septic shock Effects 0.000 claims abstract description 3
- 231100000872 sexual dysfunction Toxicity 0.000 claims abstract description 3
- 208000010228 Erectile Dysfunction Diseases 0.000 claims abstract 2
- 206010021138 Hypovolaemic shock Diseases 0.000 claims abstract 2
- 206010007625 cardiogenic shock Diseases 0.000 claims abstract 2
- 201000001881 impotence Diseases 0.000 claims abstract 2
- 206010040560 shock Diseases 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 98
- 239000001257 hydrogen Substances 0.000 claims description 96
- 229910052739 hydrogen Inorganic materials 0.000 claims description 96
- 125000001072 heteroaryl group Chemical group 0.000 claims description 82
- 125000003118 aryl group Chemical group 0.000 claims description 73
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 60
- 150000002431 hydrogen Chemical class 0.000 claims description 60
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 59
- 150000001413 amino acids Chemical class 0.000 claims description 43
- COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 claims description 39
- 125000004429 atom Chemical group 0.000 claims description 34
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 33
- 150000001336 alkenes Chemical class 0.000 claims description 31
- 125000001475 halogen functional group Chemical group 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 150000001345 alkine derivatives Chemical class 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 19
- 125000002252 acyl group Chemical group 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 102000001189 Cyclic Peptides Human genes 0.000 claims description 16
- 108010069514 Cyclic Peptides Proteins 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 125000006413 ring segment Chemical group 0.000 claims description 14
- 125000000539 amino acid group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 241001465754 Metazoa Species 0.000 claims description 9
- 125000002619 bicyclic group Chemical group 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 150000003573 thiols Chemical class 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 238000012412 chemical coupling Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- 150000002475 indoles Chemical class 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 1
- 230000003542 behavioural effect Effects 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 25
- 230000006399 behavior Effects 0.000 abstract description 3
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- 102000005962 receptors Human genes 0.000 description 70
- 108020003175 receptors Proteins 0.000 description 70
- 230000015572 biosynthetic process Effects 0.000 description 51
- 238000003786 synthesis reaction Methods 0.000 description 51
- 108090000765 processed proteins & peptides Proteins 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 235000001014 amino acid Nutrition 0.000 description 47
- 229940024606 amino acid Drugs 0.000 description 47
- -1 oxygen radical Chemical class 0.000 description 43
- 239000000203 mixture Substances 0.000 description 41
- 239000000243 solution Substances 0.000 description 36
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 102000004196 processed proteins & peptides Human genes 0.000 description 18
- 125000004122 cyclic group Chemical group 0.000 description 16
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 15
- 125000005842 heteroatom Chemical group 0.000 description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- 229920005989 resin Polymers 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 238000007363 ring formation reaction Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000002552 dosage form Substances 0.000 description 11
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- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 9
- 125000003974 3-carbamimidamidopropyl group Chemical group C(N)(=N)NCCC* 0.000 description 9
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 241000124008 Mammalia Species 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 9
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
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- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 7
- 101000978422 Homo sapiens Melanocortin receptor 5 Proteins 0.000 description 7
- 102100023723 Melanocortin receptor 5 Human genes 0.000 description 7
- 125000004442 acylamino group Chemical group 0.000 description 7
- 125000004104 aryloxy group Chemical group 0.000 description 7
- 238000010511 deprotection reaction Methods 0.000 description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 description 7
- 235000018102 proteins Nutrition 0.000 description 7
- 102000004169 proteins and genes Human genes 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 6
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
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- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 6
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 6
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- 238000004949 mass spectrometry Methods 0.000 description 6
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- 239000011734 sodium Substances 0.000 description 6
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- 108010072151 Agouti Signaling Protein Proteins 0.000 description 5
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
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- 238000005259 measurement Methods 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
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- Hematology (AREA)
- Gynecology & Obstetrics (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Communicable Diseases (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pregnancy & Childbirth (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12667399P | 1999-03-29 | 1999-03-29 | |
| PCT/US2000/007473 WO2000058361A1 (en) | 1999-03-29 | 2000-03-21 | Melanocortin receptor ligands |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA01009881A true MXPA01009881A (es) | 2002-05-06 |
Family
ID=22426131
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA01009881A MXPA01009881A (es) | 1999-03-29 | 2000-03-21 | Ligandos de receptores de melanocortina. |
Country Status (34)
| Country | Link |
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| US (2) | US6613874B1 (zh) |
| EP (1) | EP1165613B1 (zh) |
| JP (1) | JP2002542159A (zh) |
| KR (2) | KR100519201B1 (zh) |
| CN (1) | CN1249086C (zh) |
| AR (1) | AR023201A1 (zh) |
| AT (1) | ATE393783T1 (zh) |
| AU (1) | AU763510B2 (zh) |
| BR (1) | BR0009497A (zh) |
| CA (1) | CA2368431C (zh) |
| CO (1) | CO5170531A1 (zh) |
| CZ (1) | CZ20013407A3 (zh) |
| DE (1) | DE60038734T2 (zh) |
| DK (1) | DK1165613T3 (zh) |
| ES (1) | ES2304345T3 (zh) |
| HK (1) | HK1044954B (zh) |
| HU (1) | HUP0202203A3 (zh) |
| ID (1) | ID30262A (zh) |
| IL (1) | IL145406A0 (zh) |
| MA (1) | MA25403A1 (zh) |
| MX (1) | MXPA01009881A (zh) |
| MY (1) | MY126585A (zh) |
| NO (1) | NO20014568L (zh) |
| NZ (1) | NZ514141A (zh) |
| PE (1) | PE20001641A1 (zh) |
| PL (1) | PL350095A1 (zh) |
| PT (1) | PT1165613E (zh) |
| RU (1) | RU2213098C2 (zh) |
| SA (1) | SA00210192B1 (zh) |
| SK (1) | SK13082001A3 (zh) |
| TR (1) | TR200102765T2 (zh) |
| TW (1) | TWI250990B (zh) |
| WO (1) | WO2000058361A1 (zh) |
| ZA (1) | ZA200107411B (zh) |
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2000
- 2000-03-21 ID IDW00200102111A patent/ID30262A/id unknown
- 2000-03-21 EP EP00919500A patent/EP1165613B1/en not_active Expired - Lifetime
- 2000-03-21 KR KR10-2001-7012436A patent/KR100519201B1/ko not_active IP Right Cessation
- 2000-03-21 HU HU0202203A patent/HUP0202203A3/hu unknown
- 2000-03-21 MX MXPA01009881A patent/MXPA01009881A/es active IP Right Grant
- 2000-03-21 CZ CZ20013407A patent/CZ20013407A3/cs unknown
- 2000-03-21 RU RU2001128890/04A patent/RU2213098C2/ru not_active IP Right Cessation
- 2000-03-21 KR KR1020047019303A patent/KR100558131B1/ko not_active IP Right Cessation
- 2000-03-21 IL IL14540600A patent/IL145406A0/xx unknown
- 2000-03-21 BR BR0009497-8A patent/BR0009497A/pt not_active IP Right Cessation
- 2000-03-21 ES ES00919500T patent/ES2304345T3/es not_active Expired - Lifetime
- 2000-03-21 CN CNB008057540A patent/CN1249086C/zh not_active Expired - Fee Related
- 2000-03-21 NZ NZ514141A patent/NZ514141A/xx unknown
- 2000-03-21 AT AT00919500T patent/ATE393783T1/de not_active IP Right Cessation
- 2000-03-21 JP JP2000608653A patent/JP2002542159A/ja active Pending
- 2000-03-21 DE DE60038734T patent/DE60038734T2/de not_active Expired - Fee Related
- 2000-03-21 AU AU40179/00A patent/AU763510B2/en not_active Ceased
- 2000-03-21 PL PL00350095A patent/PL350095A1/xx not_active Application Discontinuation
- 2000-03-21 SK SK1308-2001A patent/SK13082001A3/sk unknown
- 2000-03-21 PT PT00919500T patent/PT1165613E/pt unknown
- 2000-03-21 TR TR2001/02765T patent/TR200102765T2/xx unknown
- 2000-03-21 CA CA002368431A patent/CA2368431C/en not_active Expired - Fee Related
- 2000-03-21 DK DK00919500T patent/DK1165613T3/da active
- 2000-03-21 WO PCT/US2000/007473 patent/WO2000058361A1/en not_active Application Discontinuation
- 2000-03-27 MY MYPI20001220A patent/MY126585A/en unknown
- 2000-03-28 CO CO00022068A patent/CO5170531A1/es not_active Application Discontinuation
- 2000-03-28 TW TW089105726A patent/TWI250990B/zh not_active IP Right Cessation
- 2000-03-29 AR ARP000101405A patent/AR023201A1/es active IP Right Grant
- 2000-03-29 US US09/537,789 patent/US6613874B1/en not_active Expired - Fee Related
- 2000-03-29 PE PE2000000267A patent/PE20001641A1/es not_active Application Discontinuation
- 2000-06-26 SA SA00210192A patent/SA00210192B1/ar unknown
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2001
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- 2001-09-20 NO NO20014568A patent/NO20014568L/no not_active Application Discontinuation
- 2001-09-26 MA MA26340A patent/MA25403A1/fr unknown
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